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From the Bicyclo[3.3.0]octane Framework to Multiply Bridged [12]Annulenes and Semibulvanes

Authors

  • Dr. Harald Kohnz,

    1. Institut für Organische Chemie der Universität Johann-Joachim-Becher-Weg 18-22, D-6500 Mainz 1 (FRG)
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  • Dipl.-Chem. Bernhard Düll,

    1. Institut für Organische Chemie der Universität Johann-Joachim-Becher-Weg 18-22, D-6500 Mainz 1 (FRG)
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  • Prof. Dr. Klaus Müllen

    Corresponding author
    1. Institut für Organische Chemie der Universität Johann-Joachim-Becher-Weg 18-22, D-6500 Mainz 1 (FRG)
    • Institut für Organische Chemie der Universität Johann-Joachim-Becher-Weg 18-22, D-6500 Mainz 1 (FRG)
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  • This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

Abstract

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The title compounds 2 and 3 are of great importance in terms of bonding theory. They were synthesized from the readily accessible precursor 1. The 4nπ species 2 allows comparison of its bonding with that in analogous [14]-, [16]-, and [18]annulenes. Compound 3 is the first doubly bridged semibullvalene; the degenerate Cope rearrangement is accelerated by the bridges (E [DOUBLE BOND] CO2Et).

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